NO864474L - Nye 4-benzyl-1-(2h)-ftalazinon-derivater. - Google Patents
Nye 4-benzyl-1-(2h)-ftalazinon-derivater.Info
- Publication number
- NO864474L NO864474L NO864474A NO864474A NO864474L NO 864474 L NO864474 L NO 864474L NO 864474 A NO864474 A NO 864474A NO 864474 A NO864474 A NO 864474A NO 864474 L NO864474 L NO 864474L
- Authority
- NO
- Norway
- Prior art keywords
- residue
- formula
- acid
- group
- benzyl
- Prior art date
Links
- -1 C2-C6-alkanoyloxy Chemical group 0.000 claims abstract description 31
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
- 239000000460 chlorine Chemical group 0.000 claims abstract description 11
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 9
- 239000011737 fluorine Substances 0.000 claims abstract description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 8
- JUCCMEHWBGPJKS-UHFFFAOYSA-N 4-benzyl-2h-phthalazin-1-one Chemical class C12=CC=CC=C2C(=O)NN=C1CC1=CC=CC=C1 JUCCMEHWBGPJKS-UHFFFAOYSA-N 0.000 claims abstract description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 230000008569 process Effects 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 48
- 239000002253 acid Substances 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 19
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- 230000010933 acylation Effects 0.000 claims description 8
- 238000005917 acylation reaction Methods 0.000 claims description 8
- 238000005804 alkylation reaction Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 230000029936 alkylation Effects 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002130 sulfonic acid ester group Chemical group 0.000 claims description 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract description 3
- 230000003266 anti-allergic effect Effects 0.000 abstract description 3
- 150000002431 hydrogen Chemical class 0.000 abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 50
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 46
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
- 239000000243 solution Substances 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 28
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 24
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- 238000003756 stirring Methods 0.000 description 22
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- 239000000126 substance Substances 0.000 description 20
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 17
- 239000013543 active substance Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000003513 alkali Substances 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 11
- 239000005711 Benzoic acid Substances 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 239000000155 melt Substances 0.000 description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
- 229910021529 ammonia Inorganic materials 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000012458 free base Substances 0.000 description 6
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical group C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical group 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 208000006673 asthma Diseases 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 229920002261 Corn starch Polymers 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
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- 150000002148 esters Chemical class 0.000 description 4
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
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- 239000005457 ice water Substances 0.000 description 4
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- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3539873 | 1985-11-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO864474D0 NO864474D0 (no) | 1986-11-10 |
| NO864474L true NO864474L (no) | 1987-05-12 |
Family
ID=6285623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO864474A NO864474L (no) | 1985-11-11 | 1986-11-10 | Nye 4-benzyl-1-(2h)-ftalazinon-derivater. |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4841047A (da) |
| EP (1) | EP0222191B1 (da) |
| JP (1) | JPH0780871B2 (da) |
| CN (1) | CN86107627A (da) |
| AT (1) | ATE60598T1 (da) |
| AU (1) | AU593593B2 (da) |
| CA (1) | CA1295613C (da) |
| DD (1) | DD263058A5 (da) |
| DE (1) | DE3677322D1 (da) |
| DK (1) | DK172076B1 (da) |
| ES (1) | ES2031813T3 (da) |
| FI (1) | FI88504C (da) |
| GR (1) | GR3001412T3 (da) |
| HU (1) | HU196793B (da) |
| IE (1) | IE59056B1 (da) |
| IL (1) | IL80560A0 (da) |
| NO (1) | NO864474L (da) |
| PT (1) | PT83713B (da) |
| SU (1) | SU1454251A3 (da) |
| ZA (1) | ZA868531B (da) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU609210B2 (en) * | 1987-11-13 | 1991-04-26 | Viatris Gmbh & Co. Kg | Azelastine embonate, processes for its preparation and pharmaceutical formulations which contain azelastine embonate as active substance |
| EP0322153A3 (en) * | 1987-12-21 | 1990-08-16 | Pfizer Inc. | Heterocyclic oxophtalazinyl acetic acids |
| FR2643373B1 (fr) * | 1989-01-10 | 1993-12-31 | Adir Cie | Nouveaux derives des bisarylalcenes, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
| DK0396069T3 (da) * | 1989-05-05 | 1994-07-25 | Asta Medica Ag | Salte af azelastin med forbedret opløselighed |
| JPH04198180A (ja) * | 1990-11-28 | 1992-07-17 | Eezai Kagaku Kk | ベンジルフタラゾン誘導体の製造方法 |
| DE4207234A1 (de) * | 1992-03-07 | 1993-09-09 | Asta Medica Ag | Neue aminocarbonsaeure-derivate mit antiallergischer/antiasthmatischer wirkung und verfahren zu deren herstellung |
| EP0561166A1 (de) * | 1992-03-17 | 1993-09-22 | ASTA Medica Aktiengesellschaft | Dosieraerosole enthaltend den Wirkstoff D-18024 und verwandte Strukturen |
| CZ199593A3 (en) * | 1992-10-02 | 1994-04-13 | Asta Medica Ag | Phthalazinone derivatives exhibiting anti-arrhythmic and analgesic activity and eliminating resistance to a plurality of medicaments (mdr) |
| US7151102B2 (en) * | 2000-10-30 | 2006-12-19 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
| DE60335359D1 (de) * | 2002-04-30 | 2011-01-27 | Kudos Pharm Ltd | Phthalazinonderivate |
| GB0305681D0 (en) | 2003-03-12 | 2003-04-16 | Kudos Pharm Ltd | Phthalazinone derivatives |
| US7449464B2 (en) * | 2003-03-12 | 2008-11-11 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
| GB0419072D0 (en) | 2004-08-26 | 2004-09-29 | Kudos Pharm Ltd | Phthalazinone derivatives |
| JP5607291B2 (ja) | 2004-11-24 | 2014-10-15 | メダ ファーマシューティカルズ インコーポレイテッド | アゼラスチンを含む組成物およびその使用方法 |
| US8758816B2 (en) | 2004-11-24 | 2014-06-24 | Meda Pharmaceuticals Inc. | Compositions comprising azelastine and methods of use thereof |
| US20070020330A1 (en) * | 2004-11-24 | 2007-01-25 | Medpointe Healthcare Inc. | Compositions comprising azelastine and methods of use thereof |
| GB0428111D0 (en) * | 2004-12-22 | 2005-01-26 | Kudos Pharm Ltd | Pthalazinone derivatives |
| GB0521373D0 (en) * | 2005-10-20 | 2005-11-30 | Kudos Pharm Ltd | Pthalazinone derivatives |
| US20080039444A1 (en) * | 2006-04-20 | 2008-02-14 | Glaxo Group Limited | Compounds |
| US20090181951A1 (en) * | 2006-06-15 | 2009-07-16 | Kudos Pharmaceuticals Limited | Parp inhibitors |
| WO2007144639A1 (en) * | 2006-06-15 | 2007-12-21 | Kudos Pharmaceuticals Limited | 2 -oxybenzamide derivatives as parp inhibitors |
| US20090281086A1 (en) * | 2006-06-15 | 2009-11-12 | Kudos Pharmaceuticals Limited | 2 -oxyheteroarylamide derivatives as parp inhibitors |
| UY30639A1 (es) * | 2006-10-17 | 2008-05-31 | Kudos Pharm Ltd | Derivados sustituidos de 2h-ftalazin-1-ona, sus formas cristalinas, proceso de preparacion y aplicaciones |
| US20100184770A1 (en) * | 2006-12-20 | 2010-07-22 | Glaxo Group Limited | Compounds |
| US20080280910A1 (en) * | 2007-03-22 | 2008-11-13 | Keith Allan Menear | Phthalazinone derivatives |
| TW200900396A (en) * | 2007-04-10 | 2009-01-01 | Kudos Pharm Ltd | Phthalazinone derivatives |
| US20090023727A1 (en) * | 2007-07-05 | 2009-01-22 | Muhammad Hashim Javaid | Phthalazinone derivatives |
| MX2010002749A (es) | 2007-09-14 | 2010-06-25 | Astrazeneca Ab | Derivados de ftalazinona. |
| ATE525370T1 (de) * | 2007-10-11 | 2011-10-15 | Glaxo Group Ltd | Phthalazin- und pyridoä3,4- düpyridazinverbindungen als h1-rezeptor- antagonisten |
| CA2702429A1 (en) * | 2007-10-17 | 2009-04-23 | Kudos Pharmaceuticals Limited | Crystalline form l 4-[3-(4-cyclopropanecarbonyl-piperazine-1-carbonyl)-4-fluoro-benzyl]-2h-phthalazin-1-one |
| UY31603A1 (es) | 2008-01-23 | 2009-08-31 | Derivados de ftalazinona | |
| CA2737400C (en) * | 2008-10-07 | 2016-11-22 | Astrazeneca Uk Limited | Pharmaceutical formulation 514 |
| US20110015393A1 (en) * | 2009-07-15 | 2011-01-20 | Astrazeneca Ab | Phthalazinone compound |
| CN113956239A (zh) * | 2021-10-28 | 2022-01-21 | 昆明源瑞制药有限公司 | 一种盐酸氮卓斯汀及其制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3017411A (en) * | 1962-01-16 | New substituted phthalazones and proc- | ||
| DE2114884A1 (de) * | 1971-03-27 | 1972-10-12 | Cassella Farbwerke Mainkur Ag, 6000 Frankfurt | Basisch substituierte Derivate des 1(2H)-Phthalazinons |
| US3813384A (en) * | 1972-01-17 | 1974-05-28 | Asta Werke Ag Chem Fab | Basically substituted benzyl phthalazone derivatives,acid salts thereof and process for the production thereof |
| EP0174464B1 (de) * | 1984-09-14 | 1990-01-03 | ASTA Pharma AG | Substituierte Benzylphthalazinon-Derivate |
| DE3530793A1 (de) * | 1984-09-14 | 1986-03-27 | Asta-Werke Ag Chemische Fabrik, 4800 Bielefeld | Substituierte benzylphthalazinon-derivate |
-
1986
- 1986-10-15 ES ES198686114241T patent/ES2031813T3/es not_active Expired - Lifetime
- 1986-10-15 AT AT86114241T patent/ATE60598T1/de active
- 1986-10-15 DE DE8686114241T patent/DE3677322D1/de not_active Expired - Lifetime
- 1986-10-15 EP EP86114241A patent/EP0222191B1/de not_active Expired - Lifetime
- 1986-11-06 SU SU864028445A patent/SU1454251A3/ru active
- 1986-11-10 FI FI864555A patent/FI88504C/fi not_active IP Right Cessation
- 1986-11-10 NO NO864474A patent/NO864474L/no unknown
- 1986-11-10 IE IE296086A patent/IE59056B1/en not_active IP Right Cessation
- 1986-11-10 CA CA000522580A patent/CA1295613C/en not_active Expired - Lifetime
- 1986-11-10 ZA ZA868531A patent/ZA868531B/xx unknown
- 1986-11-10 DD DD86296130A patent/DD263058A5/de unknown
- 1986-11-10 DK DK536486A patent/DK172076B1/da active
- 1986-11-10 PT PT83713A patent/PT83713B/pt not_active IP Right Cessation
- 1986-11-10 US US06/928,458 patent/US4841047A/en not_active Expired - Fee Related
- 1986-11-10 IL IL80560A patent/IL80560A0/xx unknown
- 1986-11-10 AU AU64982/86A patent/AU593593B2/en not_active Ceased
- 1986-11-10 HU HU864642A patent/HU196793B/hu not_active IP Right Cessation
- 1986-11-10 CN CN198686107627A patent/CN86107627A/zh active Pending
- 1986-11-11 JP JP61266808A patent/JPH0780871B2/ja not_active Expired - Lifetime
-
1991
- 1991-01-31 GR GR91400092T patent/GR3001412T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2031813T3 (es) | 1993-01-01 |
| FI88504B (fi) | 1993-02-15 |
| DK536486A (da) | 1987-05-12 |
| IL80560A0 (en) | 1987-02-27 |
| HU196793B (en) | 1989-01-30 |
| IE862960L (en) | 1987-05-11 |
| NO864474D0 (no) | 1986-11-10 |
| ZA868531B (en) | 1987-07-29 |
| GR3001412T3 (en) | 1992-09-25 |
| CA1295613C (en) | 1992-02-11 |
| FI88504C (fi) | 1993-05-25 |
| IE59056B1 (en) | 1993-12-15 |
| EP0222191B1 (de) | 1991-01-30 |
| JPS62114987A (ja) | 1987-05-26 |
| FI864555A0 (fi) | 1986-11-10 |
| DK172076B1 (da) | 1997-10-13 |
| AU593593B2 (en) | 1990-02-15 |
| AU6498286A (en) | 1987-05-14 |
| DE3677322D1 (de) | 1991-03-07 |
| SU1454251A3 (ru) | 1989-01-23 |
| FI864555A7 (fi) | 1987-05-12 |
| DK536486D0 (da) | 1986-11-10 |
| DD263058A5 (de) | 1988-12-21 |
| PT83713B (pt) | 1989-06-30 |
| CN86107627A (zh) | 1987-07-15 |
| PT83713A (de) | 1986-12-01 |
| HUT42084A (en) | 1987-06-29 |
| US4841047A (en) | 1989-06-20 |
| ATE60598T1 (de) | 1991-02-15 |
| EP0222191A1 (de) | 1987-05-20 |
| JPH0780871B2 (ja) | 1995-08-30 |
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